An individual makes a capital gain on the sale of a commercial property and invests the proceeds by buying shares in a private company in a qualifying trade. Can rollover relief be claimed? 

Arthur Weller replies:  

I am assuming that you are talking about a commercial property that was rented out to someone else, and from which the owner received rental income. If so, the answer to your question is that there is generally no rollover relief on the disposal of a commercial investment property, except in the case of a compulsory purchase. But if you are talking about a commercial property that the individual used in their own business, then rollover (or holdover) relief can be available on its disposal. But only when the reinvestment is in a new business asset used by the individual for their business. Shares in a company are not qualifying assets for reinvestment.